Enjoy Old Town Charm in Motomachi-Ishikawacho
Probably the most charming of all shotengai is this one in Yokohama, just a little over 30 minutes from Tokyo's famous Shibuya. If you decide to get off JR Ishikawacho, you will pass by the less posh parts of the shopping street: the ones that boast great bargains like this ceramics shop with Japan-made items for as low as ¥100! If you'd like to take home some saucers, glass coasters, teapots or even nabe pots, this family-owned Matsumoto shop is the place to be.
Walk a little further and you'll hit Portier Coffee, where you could shop for good coffee, and then start your street shopping journey in Motomachi. Motomachi has expensive brands like Swarovski, Rimowa, Tommy Hilfiger and Brooks Brothers, but you could also score exclusive buys from Japanese brands such as Kitamura, where you can get handcrafted Japanese leather goods. In Motomachi, you'll feel transported to the streets of Europe. In February, you can enjoy great bargains during the Charming Sale, but on regular days, you might be in for a surprise too, like Disney-Princess-look-a-likes serenading you.
Shop Hop & Culture Trip in Jiyugaoka
The streets of Jiyugaoka are worth exploring even without the intention to shop. There are amazing cafés like Peter Rabbit Garden Cafe, Jiyugaoka Bakeshop, and Latte Graphic, which are good stopovers before or after shopping. Most of Jiyugaoka is on the high-end side, but if you carefully explore all the alleys, you may end up in novelty shops, an Italian-brand outlet store (a good place to shop for formal wear), and my go-to shop for a great selection of pre-loved items, where I scored an Issey Miyake skirt for ¥8,000 (US$71) and a Missoni dress for ¥12,000 (US$106). If you are very familiar with Japanese celebrities, you might even spot one there as that's where several live. And do not leave the shopping street without passing by Kosoan, a traditional tea house in a 100-year-old wooden home.
Hunt for Deals Under the Kanda Train Tracks
Kanda is not necessarily a posh neighborhood, but it is still in one of the prime areas of Tokyo. In Kanda Manseibashi, with a little luck, you can score a collector's item like a Vintage Pentax Film Camera for ¥10,000 (US$89) only. If there's any reason to go to this area, it's the retail design of this shopping street where shops are lined under a repurposed railway. Here, you can find an amazing selection of bespoke Japanese brands and only-in-Japan modern handcrafted merchandise (not the usual chopsticks or traditional pottery) from home items to jackets, to bags, to leather items. This is the perfect place to find souvenirs that are not overrated. Oh, and if you love booze, Devilcraft in the same area is the best stopover you could make. Craft beer lovers in Tokyo head to this place after a long day at work or good shopping in Kanda.
Shop Like a Local on Bremen Dori in Motosumiyoshi
Motosumiyoshi is the neighboring station of the posh neighborhood of Musashi-Kosugi. While spacious and modern shopping malls are in Musashi-Kosugi, its neighbor, Motosumiyoshi has old-school shopping streets where you could find a lot of bargains. Noteworthy places to visit include the drugstores with cheaper prices than usual chains Tomod's or Matsumoto Kiyoshi. There are also supermarkets that sell cheaper stuff than your usual grocery shops. If you want imported finds, including gluten-free goodies or cheap caviar (I got a cupful of caviar for ¥300!), Galleon Shop is a place you shouldn't miss.
Explore Tokyo's 'Old Shibuya' in Kamata
Kamata may not have a stellar reputation nowadays but history will tell you that it once had the "trendsetter center" reputation Shibuya enjoys today. It used to dictate the fashion trends in the city, thanks to its label as a "film town," because it cradled the once famous Shochiku Studios, founded by the oldest company in Japan involved in film production (incepted in 1895). The shotengai right across JR Kamata Station has everything you need, from pantry items to ceramics and clothing. A noteworthy place to visit is Shimamura, where you can find the best buys for winter goods (which can be expensive elsewhere) such as thick blankets, fleece bed covers, heat-tech garments (yes, cheaper than Uniqlo), and more.
From another station, Keikyu-Kamata, is an equally worthy shotengai where really cheap overruns are sold, making it a good place to buy items in bulk, ideal for reselling or serious souvenir shopping. Before or after shopping, there's actually more to enjoy in Kamata such as a black water hot spring bath (said to be good for the skin), a really good tonkatsu pork cutlet in Aoki, some retro film-watching in Theatre Kamata, a bite of the local's top kara-age choice (Torikyu), and a lazy lounge in the "Godzilla park" (Tire Park).